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alpha-Amidation of cyclic ethers catalyzed by simple copper salt and a mild and efficient preparation method for alpha,omega-amino alcohols

Copper(II) trifluoromethanesulfonate catalyzed the amidation of cyclic ethers with iminoiodanes under mild conditions (CH2Cl2, 40C) with good yields (up to 86% based on 97% conversion) and selectivity (only alpha-amino products were found). Subsequently, the tosylamidated products could undergo a reductive ring-opening reaction to give alpha,omega-amino alcohols.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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SELECTIVE CLEAVAGE OF ETHERS BY SODIUM IODIDE – ACYL CHLORIDE

Cyclic and acyclic ethers are regioselectively cleavaged at less substituted alpha-carbon-oxygen bond in the absence of Lewis acid by the reagent system of sodium iodide and acyl chlorides.

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Tetrahydrofuran – Wikipedia,
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STRUCTURE AND FORMATION OF C4H7O(1+) IONS RESULTING FROM ELECTRON IMPACT INDUCED DECOMPOSITION OF CYCLIC PRECURSORS

Possible structures and modes of formation of C4H7O(1+) ions formed by electron impact induced decomposition of tetrahydrofuran and tetrahydropyran derivates are discussed in view of labelling results and MIKE, CA, and T data.Limitations of these techniques are pointed out.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Oxidative transformation of cyclic ethers/amines to lactones/lactams using a DIB/TBHP protocol

A novel C-H oxidation of cyclic ethers and amines to the corresponding lactones and lactams was developed using a DIB/TBHP protocol. The reaction is mild and no metallic reagent is involved. In addition, study shows that the electronic properties of the substituents could affect the selectivity of oxidation. The Royal Society of Chemistry 2013.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Nafion-H catalyzed acetylation of alcohols

A wide variety of alcohols, some containing acid sensitive groups also, underwent smooth acetylation with acetic anhydride upon catalysis with Nation-H, a solid acid catalyst, which could be recovered and used again.

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Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Anodic alpha-Methoxylation of Aliphatic Saturated Ethers

The anodic oxidation of aliphatic saturated ethers carried out in a mixed solvent of methanol and acetic acid gave alpha-methoxylated ethers in much better yields than those obtained by using only methanol as a solvent.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Synthesis of chloroesters by the cleavage of cyclic and acyclic ethers using La(NO3)3¡¤6H2O as a mild and efficient catalyst under solvent-free conditions

A mild and an efficient synthesis of chloroesters is described by the reaction of cyclic and acyclic ethers with acid chlorides in the presence of a catalytic amount of La(NO3)3¡¤6H2O under solvent-free conditions, affording the corresponding chloroesters in excellent yields. Copyright Taylor & Francis Group, LLC.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Effect of process parameters on supercritical liquefaction of Xanthium strumarium for bio-oil production

Supercritical liquefaction process is used for producing energy from biomass. The common reaction conditions for supercritical liquefaction process are the 240-380 C temperature range and 5-20 MPa pressure values range. Xanthium strumarium liquefaction experiments were performed in a cylindrical reactor (75 mL) in organic solvents (acetone, ethanol, methanol) under supercritical conditions with (zinc oxide, calcium hydroxide) and without catalyst at the temperatures of 250, 275 and 300 C. The produced liquids at 300 C in liquefaction were analyzed and characterized by Elemental, GC-MS and FT-IR. 36, 37 and 50 different types of compounds were identified by GC-MS obtained in acetone, ethanol and methanol respectively. The liquid product efficiency has been obtained at 300 C in acetone with zinc oxide catalyst (74.80%). The highest HHV value has been calculated as 32.16 MJ/kg with calcium hydroxide catalyst in acetone.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Direct Calpha-heteroarylation of structurally diverse ethers: Via a mild N -hydroxysuccinimide mediated cross-dehydrogenative coupling reaction

An important challenge in the Calpha-heteroarylation of ethers is the requirement of a large excess amount of ethers (that are used as solvents in many cases) to achieve effective transformations. This drawback has significantly restricted the Calpha-heteroarylation of ethers to the use of simple and easily accessible ether substrates. To overcome this limitation, a new, efficient, N-hydroxysuccinimide (NHS) mediated, mild and metal-free CDC strategy for the direct Calpha-heteroarylation of diverse ethers has been developed. Different to our previous benzaldehyde mediated photoredox Calpha-heteroarylation, we have identified NHS as a new and efficient mediator without using light. A distinct non-photoredox engaged hydrogen-atom-transfer (HAT) mechanism that used a nitrogen-centered radical cation produced from NHS is initially revealed. Notably, only 5-10 equivalents of ethers as coupling partners are used, which allows for structurally diverse and complex ethers to engage in this process, to create highly medicinally relevant Calpha-heteroarylated ethers. Furthermore, more structurally diverse heterocyclics can serve as reactants for this process.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Intramolecular Cyclization of Some Unsaturated Alcohols by Means of Thallium Triacetate

Reactions of some primary and secondary Delta4-, Delta5- and Delta6-alkenols with thallium triacetate (TTA) in benzene, acetic acid and chloroform as solvent have been investigated.When terminally unsubstituted Delta4-alkenols, such as 4-penten-1-ol (5a) and 5-hexen-2-ol (5b), are treated with TTA in benzene, beta-acetoxylated tetrahydrofurans 8a and 8b are obtained.However, when the reaction is carried in acetic acid the products are both regioisomers, i.e. five- and six-membered cyclic ethers (8a, 8b, 7a and 7b). 4-Methyl-4-penten-1-ol (5c) is converted in benzene into a mixture of products (8c and 7c) in which the tetrahydropyran derivative 7c is predominant, and in acetic acid it is the sole cyclization product.Terminally dialkylated alkenols, such as 5-methyl-4-hexen-1-ol (1b) and 6-methyl-5-hepten-2-ol (1c), are converted into beta-acetoxylated (4b and 4c) and unsaturated cyclic ethers (9a and 9b), in both cases of the tetrahydrofuran type. 5-Hexen-1-ol (10) and 6-hepten-1-ol (11) cyclize to the corresponding six- (13) and seven-membered cyclic ether (14), respectively.Organothallium intermediates have been isolated and identified in the cases of alcohols 5a, 5c and 10, proving that the TTA addition to the double bond has originally obeyed the Markovnikov rule. Key Words: Alcohols, unsaturated / Thallium triacetate

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem